Pour the raw sugar on a flat plate.
Cut and peel the white pith from one grapefruit. Cut the segments out of the membrane and set aside. Squeeze the membranes into a small bowl and collect any juice drippings. Zest then juice the second grapefruit.
Using one of the grapefruit peels from the segmented grapefruit, wet the very top rim of the martini glass by rubbing it on the rim. Dip the glass into the raw sugar.
Shake the vodka, 4 ounces grapefruit juice and Cointreau in a martini shaker with ice. Pour into the rimmed martini glass and garnish with grapefruit segments and grapefruit zest.
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